Skitch is bulky. Dropbox/Cloud.app are great, but too simple.

There's definitely middle ground for quick annotation, without going crazzzyyyy. If you can screenshot, annotate, and upload in 5-8 seconds, you've got my $$.

Thanks! I'll add more tools this weekend and polish it up a bit. How much would one be willing to pay for something like?

I installed a full application to do this the last time I needed annotated screenshots that didn't look like they were made by a child. I used Jing fwiw.